2-(4-iodobenzoyl)-3,5-dimethylpyrrole | 945587-86-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(4-iodobenzoyl)-3,5-dimethylpyrrole
• 英文别名: (3,5-dimethyl-1H-pyrrol-2-yl)-(4-iodophenyl)methanone
• CAS: 945587-86-0
• 化学式: C₁₃H₁₂INO
• 分子量: 325.149
• InChiKey: KDVNGVUCGJFEQP-UHFFFAOYSA-N

物化性质

• 沸点：
  383.6±42.0 °C(Predicted)
• 密度：
  1.621±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  32.9
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-(4-iodobenzoyl)-3,5-dimethylpyrrole 在 三氯化铝 、 三氟化硼乙醚 、 三乙胺 、 三氯氧磷 作用下， 以 二氯甲烷 、 甲苯 、 正戊烷 为溶剂， 反应 24.66h， 生成 1-(1,3,2-benzodioxaborol-2-yl)-2-[(Z)-(3,5-dimethyl-2H-pyrrol-2-ylidene)(4-iodophenyl)methyl]-3,5-dimethyl-1H-pyrrole
  参考文献：
  名称：

  Convenient Method To Access New 4,4-Dialkoxy- and 4,4-Diaryloxy-diaza-s-indacene Dyes:  Synthesis and Spectroscopic Evaluation

  摘要：

  A straightforward method for the synthesis of original 4,4-dialkoxy- or 4,4-diaryloxy-diaza-s-indacenes (BODIPY) derivatives obtained by treatment of BODIPY 1 with various alcohols in the presence of AlCl3 is described. The novel compounds are characterized by spectroscopic properties similar to those of the parent BODIPY 1, absorption and emission spectra with similar band shapes, high molar absorption coefficients (epsilon(lambda max) approximate to 80 000 M-1 cm(-1)), and for most of them high fluorescence quantum yields (Phi(exp) from 0.52 to 0.71). Among all of the new compounds synthesized, the dye 2h exhibits higher fluorescence quantum yield (0.71) and lifetime (4.09 ns) than compound 1 and a good chemical stability toward conditions compatible with biological cell-based assays.

  DOI：

  10.1021/jo061567m
• 作为产物：
  描述：

  2,4-二甲基吡咯 、 4-碘苯甲酰氯 在 甲基溴化镁 作用下， 以 乙醚 为溶剂， 反应 12.0h， 以81%的产率得到2-(4-iodobenzoyl)-3,5-dimethylpyrrole
  参考文献：
  名称：

  Convenient Method To Access New 4,4-Dialkoxy- and 4,4-Diaryloxy-diaza-s-indacene Dyes:  Synthesis and Spectroscopic Evaluation

  摘要：

  A straightforward method for the synthesis of original 4,4-dialkoxy- or 4,4-diaryloxy-diaza-s-indacenes (BODIPY) derivatives obtained by treatment of BODIPY 1 with various alcohols in the presence of AlCl3 is described. The novel compounds are characterized by spectroscopic properties similar to those of the parent BODIPY 1, absorption and emission spectra with similar band shapes, high molar absorption coefficients (epsilon(lambda max) approximate to 80 000 M-1 cm(-1)), and for most of them high fluorescence quantum yields (Phi(exp) from 0.52 to 0.71). Among all of the new compounds synthesized, the dye 2h exhibits higher fluorescence quantum yield (0.71) and lifetime (4.09 ns) than compound 1 and a good chemical stability toward conditions compatible with biological cell-based assays.

  DOI：

  10.1021/jo061567m

文献信息

• [EN] HIGHLY SENSITIVE DETECTION OF BIOMOLECULES USING PROXIMITY INDUCED BIOORTHOGONAL REACTIONS<br/>[FR] DÉTECTION HAUTEMENT SENSIBLE DE BIOMOLÉCULES PAR DES RÉACTIONS BIOORTHOGONALES INDUITES PAR LA PROXIMITÉ
  申请人：UNIV CALIFORNIA

  公开号：WO2016109733A1

  公开（公告）日：2016-07-07

  There provided, inter alia, reagents and methods for modulation fluorescence of a tetrazine containing compound and/or a dienophile-containing compound. There is provided a method of detecting binding of a first affinity ligand and a second affinity ligand, the method includes the follow steps. Contacting a tetrazine-containing compound with a dienophile-containing compound, the tetrazine-containing compound comprising a first affinity ligand covalently attached to a tetrazine moiety and the dienophile-containing comprising a second affinity ligand covalently attached to a dienophile moiety.

  提供了用于调节含有四氮杂环的化合物和/或含有二烯丙基的化合物荧光的试剂和方法。提供了一种检测第一亲和配体和第二亲和配体结合的方法，该方法包括以下步骤。将含有四氮杂环的化合物与含有二烯丙基的化合物接触，其中含有四氮杂环的化合物包括与四氮杂环基团共价连接的第一亲和配体，含有二烯丙基的化合物包括与二烯丙基团共价连接的第二亲和配体。
• Bioorthogonal Tetrazine-Mediated Transfer Reactions Facilitate Reaction Turnover in Nucleic Acid-Templated Detection of MicroRNA
  作者：Haoxing Wu、Brandon T. Cisneros、Christian M. Cole、Neal K. Devaraj

  DOI：10.1021/ja510839r

  日期：2014.12.31

  Tetrazine ligations have proven to be a powerful bioorthogonal technique for the detection of many labeled biomolecules, but the ligating nature of these reactions can limit reaction turnover in templated chemistry. We have developed a transfer reaction between 7-azabenzonorbornadiene derivatives and fluorogenic tetrazines that facilitates turnover amplification of the fluorogenic response in nucleic acid-templated reactions. Fluorogenic tetrazine-mediated transfer (TMT) reaction probes can be used to detect DNA and microRNA (miRNA) templates to 0.5 and 5 pM concentrations, respectively. The endogenous oncogenic miRNA target mir-21 could be detected in crude cell lysates and detected by imaging in live cells. Remarkably, the technique is also able to differentiate between miRNA templates bearing a single mismatch with high signal to background. We imagine that TMT reactions could find wide application for amplified fluorescent detection of clinically relevant nucleic acid templates.
• Synthesis and spectroscopic properties of 2-ketopyrrole–BF2 complexes: a new class of fluorescent dye
  作者：Jiong Chen、Armin Burghart、Chi-Wai Wan、Long Thai、Cesar Ortiz、Joe Reibenspies、Kevin Burgess

  DOI：10.1016/s0040-4039(00)00166-0

  日期：2000.4

  The 2-ketopyrrole complexes 3 and 4 were isolated as minor products in syntheses of the corresponding 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene (BODIPY(R)) dyes 1 and 2. Compounds 4 were shown to be highly fluorescent having emissions between 504 and 544 nm with quantum yields between 0.52 and 0.89. (C) 2000 Elsevier Science Ltd. All rights reserved.
• HIGHLY SENSITIVE DETECTION OF BIOMOLECULES USING PROXIMITY INDUCED BIOORTHOGONAL REACTIONS
  申请人：The Regents of the University of California

  公开号：US20180244643A1

  公开（公告）日：2018-08-30

  There provided, inter alia, reagents and methods for modulation fluorescence of a tetrazine containing compound and/or a dienophile-containing compound. There is provided a method of detecting binding of a first affmity ligand and a second affinity ligand, the method includes the follow steps. Contacting a tetrazine-containing compound with a dienophile-containing compound, the tetrazine-containing compound comprising a first affinity ligand covalently attached to a tetrazine moiety and the dienophile-containing comprising a second affmity ligand covalently attached to a dienophile moiety.